HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → (6R,7aS)-6-Hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | (6R,7aS)-6-(tert-Butyl-diphenyl-silanyloxy)-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one | HCID 70975953 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (6R,7aS)-6-Hydroxy-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one | HCID 70976331 | 95.2% |
Reaction Steps
Tetrabutyl ammonium fluoride (1.0 g, 3.8 mmol) was added to a solution of (6R,7aS)-6-(tert-Butyl-diphenyl-silanyloxy)-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (1.8 g, 3.3 mmol) in anhydrous THF (20 mL). The mixture was stirred for 2 hours at room temperature. The mixture was poured into water (50 mL), extracted with ethyl acetate (3×50 mL). The organic layers was combined, washed with brine (50 mL), dried over anhydrous sodium sulphate, filtered and concentrated. The residue was purified by silica gel column chromatography (MeOH/CH2Cl2=1:20) to give 0.95 g (94%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08497288B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-9d7394586766416993563a9dcfbf164d |
| Source note | uspto-grants-2013_07 |